Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

Propyl propanoate may be made in three stages, with propanenitrile as the sole organic starting material. During step 1, the nitrile is changed into compound X. During step 2, compound X is changed into compound Y. During step 3, compound Y is reacted with additional compound X to produce propyl propanoate. $\text{CH}_3\text{CH}_2\text{CN} \rightarrow X \rightarrow Y \rightarrow \text{CH}_3\text{CH}_2\text{CO}_2\text{CH}_2\text{CH}_2\text{CH}_3$ Which reagents would be suitable for step 1 and step 2?

  • Astep 1: HCl(aq); step 2: conc. $\text{H}_2\text{SO}_4$
  • Bstep 1: HCl(aq); step 2: $\text{LiAlH}_4$
  • Cstep 1: NaOH(aq); step 2: conc. $\text{H}_2\text{SO}_4$
  • Dstep 1: NaOH(aq); step 2: $\text{NaBH}_4$

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